2000

Matt Damon

November 03

Popping Ribs

Damon stars with Will Smith and Charlize Theron in the Robert Redford's The Legend of Bagger Vance. While training for the golf scenes he separates a rib. "Every time I had to swing the club, my rib would pop out again," he tells PEOPLE. "I'd swing, and Tony the chiropractor would run over and he'd put my rib back in there." In December, Damon earns a reported $5.5 million for All the Pretty Horses with Penélope Cruz (left).

2001

Matt Damon

December 07

In Good Company

Damon appears alongside George Clooney, Brad Pitt and Julia Roberts in Ocean's Eleven. The comic caper remake is a blockbuster hit, making more than $183 million during its five-month run in theaters. He also appears in the sequels, Ocean's Twelve in 2004 and Ocean's Thirteen in 2007.

2002

March

Personal Project

Stolen Summer is released. The film is the first to be spawned by Affleck's and Damon's Project Greenlight, a reality show that documents the filmmaking process. The movie, which costars Kevin Pollak, Aidan Quinn and Bonnie Hunt, is a huge flop, grossing $119,841 at the box office, according to Baseline.

Matt Damon

June 14

Lights, Camera, Action Hero

Damon makes his debut as an action hero in The Bourne Identity, for which he makes $10 million playing an assassin with amnesia. In July 2004, The Bourne Supremacy is released, and Damon pockets a reported $15 million to return as Jason Bourne in the sequel, according to PEOPLE. The third installment, Bourne Ultimatum, is released in 2007.

2004

Matt Damon

May – June

On Stage

Damon takes his first on-stage role since college with the London production of This Is Our Youth, also starring Casey Affleck. He plays Dennis Ziegler, a teenage drug dealer in New York City. "I just couldn't say no," Damon tells Newsday. Britain's Guardian calls the clean-cut Damon "horribly authentic as the cocky Dennis."

Matt Damon

July 04

In Love With Luciana

Damon brings girlfriend Luciana Barroso, a part-time bartender in Miami Beach, home to meet his family and friends in Boston. A source tells PEOPLE that Damon and Barroso met in 2003 while he was filming Stuck on You. The following year, Damon, 34, proposes to Barroso, 29, and the pair weds on Dec. 9 in a top-secret ceremony at Manhattan's City Hall. Barroso's 7-year-old daughter (from a previous marriage), Alexia, and New York City Mayor Michael Bloomberg attend the ceremony.

2006

Matt Damon

May

Giving Back

May 2006 Damon takes a trip to Africa to embark on a six-day "listening and learning trip" with his brother Kyle through AIDS-ravaged Zambia. The actor, who is expecting a baby with his wife, tells PEOPLE, "The world I leave to my daughter is going to be affected by what I do, or what I don't do. The best way to honor and love her is to do what I can, here and now."

Matt Damon

June 11

Proud Parents

Damon and his wife Luciana, welcome daughter Isabella. Damon tells PEOPLE that his 7-year-old stepdaughter Alexia would have been disappointed if the baby was a boy. "She definitely wanted a sister," the new dad says. In August 2008, the Damon's welcome their second child together, daughter Gia Zavala.

October 13

Reel Drama

The Departed, a crime drama that stars Damon, Nicholson, Leonardo DiCaprio and Mark Wahlberg, is released in theatres. Entertainment Weekly Damon's performance as a gangster that has slipped into the police force "career-defining." Before the year ends, her delivers more critically acclaimed work in Robert DeNiro's The Good Shepherd with Angelina Jolie.

2007

Matt Damon

November

The Sexiest Man Alive

After years of honorable mentions, Damon is finally named PEOPLE's Sexiest Man Alive in 2007. Friend and costar George Clooney – who has been named twicehas long advocated for Damon's win, telling PEOPLE in 2006, "If you've been around him, you know he's sexy. His eyes pop. They have a twinkle. He's got a good smile. He's quite the dancer. He does rock a Speedo in Ocean's 13." Damon says of the honor, "You've given an aging suburban dad the ego-boost of a lifetime."

Photo Credits

BIOGRAPHY (top to bottom): Everett Collection; Bob Marshak/Warner Bros.; UNIVERSAL/KOBAL; NILS JORGENSEN/REX USA; ALLOCCA FERREIRA/STARTRAKS; J. TAYLOE EMERY; RAMEY

Edited by Mai Dinh, Janet Murphy